Reader’s Dilemma: How Can I Reconnect With a College Crush?

The older I get, the more I kick myself for all the times I was afraid to take a chance with a guy back in my younger days. So when I saw this reader question this morning, I immediately wanted to give her the push I never gave myself.

She writes:

Hi Gena! Given your awesome posts I trust you won't judge me as harshly as I judge myself on this one. I graduated college a few years ago, and six months ago relocated to the city I went to school in. And because Facebook is psychic/conniving, once I moved back to my current city I started seeing more posts on my newsfeed from other alum who live here-in particular a guy I had a few classes with back in the day. Long story short, I've wound up with a bit of a crush on this guy (who, for the record, frequently "likes" and comments on my updates and such) but don't have any rational excuse to run into him. Would it be super weird to ask him out over Facebook? Do people even do that? I'm worried it could be creepy or awkward but then again, anything remotely internet-dating-like is totally new for me. Help!

Sincerest thanks for the flattery (blush!), but whoa girl, what’s to judge here? You saw a cute guy you used to know, you both conveniently live in the same city, and you think it would be cool to try to date him? You crazy irrational person! Seriously, I sometimes still try to google stalk my high school crush who does not ever show up in my social media and also, is married I think, so .your question is not even a little creepy or awkward.

And, I say go for it--immediately if not sooner, before you lose your nerve. Don’t overthink it. He’s interacting with you by liking and commenting, so you’re obviously on his radar and he’s into communicating with you. Is that a guarantee he’ll want to go out? No, but that’s a risk you have to take in life.

To minimize potential embarrassment if he’s not into it, I’d keep things on the casual side. Casual, but not vague. By which I mean, you don’t have to formally say, “Would you like to go on a date with me?” if that makes you feel too forward (although it’s not, really), but don’t go the other extreme and ask him to meet up with you and some other old college friends at a rowdy bar, so he doesn’t know if your intention is just to be pals. I recommend shooting him a message, privately obvs, and saying something like, “Hey! Now that I’m back in the city, we should hang out and catch up on what we’ve been up to since the days of Psych 200. Would you be up for grabbing a drink sometime next week?” That leaves him plenty of room to gently decline if he's not into it. If that's the case, just give yourself a little time to nurse your ego by blocking him from your Facebook feed for a while, and feel good that you tried.

But on the other hand, if he says yes, you'll be all set up for some one-on-one time where you can make your interest clear. Plus, he'll probably be in awe of how confident you are. Good luck, and let us know how it goes!

I mean, everyone agrees she should just go for it, right? But please, give her specific tips if you have another idea of how she should do it or what she should say!